Modulation of Oral Bioavailability and Metabolism for Closely Related Cyclic Hexapeptides

[1]  Chad E. Townsend,et al.  Passive Membrane Permeability in Cyclic Peptomer Scaffolds Is Robust to Extensive Variation in Side Chain Functionality and Backbone Geometry. , 2016, Journal of medicinal chemistry.

[2]  Matthew R. Naylor,et al.  Stereochemistry Balances Cell Permeability and Solubility in the Naturally Derived Phepropeptin Cyclic Peptides. , 2016, ACS medicinal chemistry letters.

[3]  Claudia S Neuhaus,et al.  When barriers ignore the "rule-of-five". , 2016, Advanced drug delivery reviews.

[4]  H. Roth,et al.  Pharmacokinetic Studies around the Mono‐ and Difunctionalization of a Bioavailable Cyclic Decapeptide Scaffold , 2016, ChemMedChem.

[5]  Hans-Jörg Roth,et al.  Design and Development of a Cyclic Decapeptide Scaffold with Suitable Properties for Bioavailability and Oral Exposure , 2016, ChemMedChem.

[6]  S. Vajda,et al.  Quantifying the chameleonic properties of macrocycles and other high-molecular-weight drugs. , 2016, Drug discovery today.

[7]  H. Daniel,et al.  Intestinal organoids for assessing nutrient transport, sensing and incretin secretion , 2015, Scientific Reports.

[8]  F. Albericio,et al.  The effect of N-methylation of amino acids (Ac-X-OMe) on solubility and conformation: a DFT study. , 2015, Organic & biomolecular chemistry.

[9]  S. Mandlekar,et al.  Absorption and cleavage of enalapril, a carboxyl ester prodrug, in the rat intestine: in vitro, in situ intestinal perfusion and portal vein cannulation models , 2015, Biopharmaceutics & drug disposition.

[10]  T. Vorherr.  Modifying peptides to enhance permeability. , 2015, Future medicinal chemistry.

[11]  T. Vorherr,et al.  A Detailed Investigation on Conformation, Permeability and PK Properties of Two Related Cyclohexapeptides , 2015, International Journal of Peptide Research and Therapeutics.

[12]  H. Kessler,et al.  Enantiomeric cyclic peptides with different Caco-2 permeability suggest carrier-mediated transport. , 2015, Chemistry.

[13]  Matthew P Jacobson,et al.  Probing the Physicochemical Boundaries of Cell Permeability and Oral Bioavailability in Lipophilic Macrocycles Inspired by Natural Products. , 2015, Journal of medicinal chemistry.

[14]  Robert M. Harris,et al.  Improving the passive permeability of macrocyclic peptides: Balancing permeability with other physicochemical properties. , 2015, Bioorganic & medicinal chemistry.

[15]  Siegfried S. F. Leung,et al.  Cell-permeable cyclic peptides from synthetic libraries inspired by natural products. , 2015, Journal of the American Chemical Society.

[16]  David J. Craik,et al.  Rational design and synthesis of an orally bioavailable peptide guided by NMR amide temperature coefficients , 2014, Proceedings of the National Academy of Sciences.

[17]  Spiros Liras,et al.  Improving on nature: making a cyclic heptapeptide orally bioavailable. , 2014, Angewandte Chemie.

[18]  G. Goetz,et al.  EPSA: A Novel Supercritical Fluid Chromatography Technique Enabling the Design of Permeable Cyclic Peptides. , 2014, ACS medicinal chemistry letters.

[19]  Martin J. Stoermer,et al.  Cyclic Penta- and Hexaleucine Peptides without N-Methylation Are Orally Absorbed. , 2014, ACS medicinal chemistry letters.

[20]  Dima Kozakov,et al.  How Proteins Bind Macrocycles , 2014, Nature chemical biology.

[21]  M. Shalaeva,et al.  High throughput method for the indirect detection of intramolecular hydrogen bonding. , 2014, Journal of medicinal chemistry.

[22]  Richard Svensson,et al.  Impact of Stereospecific Intramolecular Hydrogen Bonding on Cell Permeability and Physicochemical Properties , 2014, Journal of medicinal chemistry.

[23]  Fabrizio Giordanetto,et al.  Macrocyclic drugs and clinical candidates: what can medicinal chemists learn from their properties? , 2014, Journal of medicinal chemistry.

[24]  D. Fairlie,et al.  Total synthesis, structure, and oral absorption of a thiazole cyclic peptide, sanguinamide A. , 2012, Organic letters.

[25]  Yizhong Zhang,et al.  Optimizing PK properties of cyclic peptides: the effect of side chain substitutions on permeability and clearance(). , 2012, MedChemComm.

[26]  Horst Kessler,et al.  Intestinal permeability of cyclic peptides: common key backbone motifs identified. , 2012, Journal of the American Chemical Society.

[27]  Matthew P. Jacobson,et al.  Predicting and improving the membrane permeability of peptidic small molecules. , 2012, Journal of medicinal chemistry.

[28]  Yizhong Zhang,et al.  On-resin N-methylation of cyclic peptides for discovery of orally bioavailable scaffolds , 2011, Nature chemical biology.

[29]  Alexander Alex,et al.  Intramolecular hydrogen bonding to improve membrane permeability and absorption in beyond rule of five chemical space , 2011 .

[30]  Charles L Brooks,et al.  Recent advances in implicit solvent-based methods for biomolecular simulations. , 2008, Current opinion in structural biology.

[31]  Horst Kessler,et al.  Improving oral bioavailability of peptides by multiple N-methylation: somatostatin analogues. , 2008, Angewandte Chemie.

[32]  Thomas Kodadek,et al.  Quantitative comparison of the relative cell permeability of cyclic and linear peptides. , 2007, Chemistry & biology.

[33]  Stephen R. Johnson,et al.  Molecular properties that influence the oral bioavailability of drug candidates. , 2002, Journal of medicinal chemistry.

[34]  P. Selzer,et al.  Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. , 2000, Journal of medicinal chemistry.

[35]  M. Karplus,et al.  A Comprehensive Analytical Treatment of Continuum Electrostatics , 1996 .

[36]  Gerhard Klebe,et al.  Comparison of Automatic Three-Dimensional Model Builders Using 639 X-ray Structures , 1994, J. Chem. Inf. Comput. Sci..

[37]  T. Richmond,et al.  Solvent accessible surface area and excluded volume in proteins. Analytical equations for overlapping spheres and implications for the hydrophobic effect. , 1984, Journal of molecular biology.

[38]  M. Karplus,et al.  CHARMM: A program for macromolecular energy, minimization, and dynamics calculations , 1983 .

[39]  T. Vorherr,et al.  Towards intracellular delivery of peptides. , 2013, Chimia.

[40]  F. Lombardo,et al.  Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. , 2001, Advanced drug delivery reviews.